반응 #4987

반응 방정식

KBr

5'-O-(p-toluenesulfonyl)thymidine

monomethylamine

monomethylamine

→

5'-Deoxy-5'-(methyl-amino)-thymidine

용매

water

반응 조건

후처리

1. 1
   기타condensed
2. 2
   기타The vessel was sealed
3. 3
   온도The vessel was cooled
4. 4
   기타to evaporate
5. 5
   기타The remaining contents of the vessel were removed
6. 6
   세척by rinsing with water
7. 7
   세척The column was washed with water until the washings
8. 8
   세척The product was then eluted with 1N aqueous ammonium hydroxide
9. 9
   기타the resulting solid chromatographed on a column (6.5×20 cm) of silica gel with methylene chloride/methanol/concentrated aqueous ammonium hydroxide (85:13:2) as the eluting solvent
10. 10
    workup.ADDITIONThe product containing fractions
11. 11
    기타A satisfactory combustion analysis could not be obtained for this material

실험 절차

5'-O-(p-toluenesulfonyl)thymidine (19.8 g, 50 mmol) was placed in a pressure vessel into which monomethylamine (250 g) was condensed. The vessel was sealed and allowed to stand at room temperature for 3 days. The vessel was cooled, opened, and the monomethylamine allowed to evaporate. The remaining contents of the vessel were removed by rinsing with water. The aqueous solution was passed through a column (6.5×20 cm) of AG50Wx8 ion-exchange resin (H+ form). The column was washed with water until the washings were neutral. The product was then eluted with 1N aqueous ammonium hydroxide. The eluent was stripped down and the resulting solid chromatographed on a column (6.5×20 cm) of silica gel with methylene chloride/methanol/concentrated aqueous ammonium hydroxide (85:13:2) as the eluting solvent. The product containing fractions were stripped down, then taken up in water and lyophilized. The product was a pale-yellow, amorphous solid (8.81 g, 69%). A satisfactory combustion analysis could not be obtained for this material.) [α]D25 (c=1.0 in water): +25.9 deg. ir (KBr): cm-1 1693, 1472, 1273, 1076. NMR (DMSO-d6): δ 1.790 (d, 3H), 2.051 (ddd, 13.4, 6.3, 3.5 hz, 1H), 2.142 (dt, 13.4, 6.9 hz, 1H), 2.314 (s, 3H), 2.658 (d, 5.5 hz, 2H), 3.775 (td, 5.3, 3.2 hz, 1H), 4.171 (dt, 6.3, 3.2 hz, 1H), 6.134 (t, 6.9 hz, 1H) and d7.639 (s, 1H).

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